Heading SouthWest (HSW) is an unsupported on-road and off-road bikepacking adventure across Portugal, completed in a single stage. A journey in search of the lost essence of cycling, crossing the country from NorthEast to SouthWest.

The 6th edition starts in BRAGANÇA, Portugal’s north-easternmost city, and ends at SAGRES — on the edge of Europe.

Two routes, one journey:
HEADING SOUTHWEST ULTRACYCLING — following our traditional format, crossing Portugal by road.
TRAVESSIA NACIONAL BIKEPACKING — the new off-road gravel route, and adventurous approach.

HSW#06 20-26 JUNE 2027, PORTUGAL.

[ REGISTRATION OPENS NOVEMBER 1ST ]

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RUMO A SUDOESTE // Departure from BRAGANÇA and finish in the edge of Europe: Cabo São Vicente, SAGRES.

TWO ROUTES // Heading SouthWest Ultracycling [road] & Travessia Nacional Bikepacking [off road] - both heading the Atlantic.

HEADING SOUTHWEST // On road cycling route with 1.000 kilometers and 18.000 meters of climbing, through the peaks of Portugal, including the Central System Mountains. Epic finale: climbing Monchique/Foia and then heading the end of Europe.

TRAVESSIA NACIONAL // Off road cycling route - designed and tested for gravel bikes - with 1.000 kilometers, 15.000 meters of climbing, and 60% off-road. The paradigm shift in in Portugal.

FOR THE COMMUNITY // Event without profit goals >> participation fee bellow the market value: 200€. Includes official HSW'27 #Cap, tracking system and live map by Follow My Challenge, as well accidents insurance according with Portuguese law.

FOCUS IN THE EXPERIENCE // Unsupported approach and no drafting, but allowed ride in group & mechanical support among riders.

GUIDELINES 2027

'The hardest line to cross is the starting line'. This page is your compass if you’re planning to join us on June 2027. Heading SouthWest is for riders seeking true adventure — resilient, self-reliant cyclists ready to take on one of the most challenging routes in Southern Europe. Here you’ll find the concept behind HSW, our values and principles and details of the registration.

See you at the starting line, seeking together the essence of cycling.

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THE ROUTE(S) 2027

From NorthEast to SouthWest of Portugal. From the surprising lands of Trás-os-Montes, across the brutal views and dramatic slopes of the Douro Valley, through the cycling paradise and Portuguese Highlands of Serra da Estrela, along the hills and false plains of Alentejo, and heading the wild Atlantic Ocean in Algarve — the HSW journey is as diverse as it is demanding.

Two routes await: Heading SouthWest [road] & Travessia Nacional [off road].

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THE LEGACY (2022-...

No medals, no podiums, no red carpets. Our generosity is rewarded on the road. Through paths you would never roam, through climbs that no peloton dares to attempt. We are seeking the lost essence of cycling, inspired by Mike Hall's The Transcontinental and by Nelson Tree's Mountain Races. It's not about how further you go, but how deep your experience is.

Five years on the edge and heading the unknown.

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WHAT IS HEADING SOUTHWEST?

Heading SouthWest is simultaneously a personal bikepacking challenge and a collective cycling adventure. An opportunity to face your physical and emotional limits while other adventurers are doing the same. It isn't a race or a competition. 'SouthWest' follows 'self-supported' approach and drafting is not allowed.

ROUTE(S) PROFILES AND TIME LIMIT

HSW'27 will start in Bragança and finish in Sagres, Algarve. There are two routes available: the on-road 'Heading SouthWest Ultracycling' and the off-road 'Travessia Nacional Bikepacking'. The on-road set route has 1.000 kilometers and around 18.000 meters of elevation gain. The off-road set route has 1.000 kilometers and approximately 15.000 meters of elevation gain Riders will have 7 days to finish the challenge.

HOW TO ARRIVE TO BRAGANÇA?

The closest airports are in Lisbon and Porto. The city of Bragança is connected by bus with the major Portuguese cities. The closest train station is Pocinho (through the magnificent Douro Valley line) - 100 km on-road away from Bragança. We will promote carpool and car sharing among riders.

WHAT DOES 'SELF SUPPORTED' MEAN?

Unsupported ultracycling seeks the essence of cycling through the spirit of adventure, independence, autonomy and equality of circumstances among all participants. It's about your experience and challenging your own limits. So makes no sense to receive help from your family and friends with resupplies, mechanical support and accommodation. You can only use the commercial services available to the public and that are available to all riders. Ride in group and mutual help (mechanical support and sharing supplies) among participants is allowed.

WHAT DOES 'NO DRAFTING' MEAN?

Drafting is not allowed: you cannot ride on the wheel of other participants, cyclists or vehicles, thus obtaining aerodynamic advantages. Ride in group is allowed. However do not forget that ride in group and drafting are not the same!

WHICH ARE THE MANDATORY ITEMS?

Helmet, reflective vest (nights and poor visibility conditions), frontal and rear lights (including a backup kit), emergency blanket. The organization assures personal insurance for accidents (expenses for treatment, repatriation, disability and death). Presence at the briefing session is mandatory (on Saturday June 19th evening).

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